The aim of the present paper is to analyze the user’s behavior in Web 2.0 through comparing statistical data from a Web 1.0 site and an online community from Web 2.0. In order to emphasize the difference between the two concepts, we have taken into consideration the following: new vs. returning visitors, visitor loyalty, length as well as the depth of the visit to the site. Analyzing the data, one can observe that the visitor loyalty, their lengthy visits to the site and the pages they view are much higher for the site built on the principles of Web 2.0, compared to the classical sites. Likewise, we developed and implemented a collaborative tagging system that allows every registered user to publish, save and label the content with the help of tags. Therefore, this can help in building a model that not only offers customized content but also adapts the site to user needs by providing a recommendation system and aggregate collective intelligence.